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Sakuranetin

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Sakuranetin
Sakuranetin
Names
IUPAC name (2S)-4′,5-Dihydroxy-7-methoxyflavan-4-one
Systematic IUPAC name (2S)-5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-4H-1-benzopyran-4-one
Other names Naringenin 7-methyl ether
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.019.073 Edit this at Wikidata
IUPHAR/BPS
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1Key: DJOJDHGQRNZXQQ-AWEZNQCLSA-N
  • InChI=1/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1Key: DJOJDHGQRNZXQQ-AWEZNQCLBK
SMILES
  • COC1=CC(=C2C(=O)CC(OC2=C1)C3=CC=C(C=C3)O)O
Properties
Chemical formula C16H14O5
Molar mass 286.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Sakuranetin is a flavan-on, the 7-methoxy derivative of naringenin, found in Polymnia fruticosa and rice, where it acts as a phytoalexin against spore germination of Pyricularia oryzae.

Glycosides

Sakuranin is the 5-O-glucoside of sakuranetin.

Metabolism

biosynthesis

Naringenin 7-O-methyltransferase uses naringenin to yield sakuranetin, with S-adenosyl-methionine as the methyl donor.

biodegradation

In compounds like 7-methoxylated flavanones like sakuranetin, demethylation followed by sulfation occur in model organism Cunninghamella elegans.

References

  1. Sakuranetin on home.ncifcrf.gov
  2. "Sakuranetin, a flavonone phytoalexin from ultraviolet-irradiated rice leaves, Kodama O., Miyakawa J., Akatsuka T., Kiyosawa S, 1992". Archived from the original on 2012-06-16. Retrieved 2009-09-11.
  3. Rakwal, Randeep; Hasegawa, Morifumi; Kodama, Osamu (1996). "A Methyltransferase for Synthesis of the Flavanone Phytoalexin Sakuranetin in Rice Leaves". Biochemical and Biophysical Research Communications. 222 (3): 732–735. doi:10.1006/bbrc.1996.0812. PMID 8651913.
  4. Ibrahim, A. R.; Galal, A. M.; Ahmed, M. S.; Mossa, G. S. (2003). "O-demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans". Chemical & Pharmaceutical Bulletin. 51 (2): 203–206. doi:10.1248/cpb.51.203. PMID 12576658. INIST 14569933.
Flavanones and their glycosides
Flavanones
O-methylated flavanones
C-methylated flavanones
Glycosides
Acetylated
Acetylated glycosides


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